Cheap flights from Canada to Chicago

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Boston (BOS)
Chicago (CHI)
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How to find the cheapest flight from
Canada to Chicago (CHI)

All the information you need to plan the best null to CHI flight in 2021: compare Canada to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
How far in advance should I book a flight from Canada to Chicago?

Users have found that booking a flight from Canada to Chicago at least 34 days early can save you up to 86% on average compared to booking a flight this week. If booking 34 days before your flight isn’t an option for you, users have found flights from Canada to Chicago for as little as C$ 436 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 590 for flights departing within the next 3 days.

What is the cheapest month to fly from Canada to Chicago?

April can be a great time to fly to Chicago from Canada with a flight ticket averaging about C$ 317. Cheapflights users have found deals in the month of April for as cheap as C$ 240. The most expensive prices can be found in the month of January.

Cheap flights from Canada to Chicago in July, August 2021

The best prices found for Canada to CHI flights for July, August
26 Aug - 29 Aug
C$ 402pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
20 Aug - 20 Sep
C$ 416pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl
24 Aug - 7 Sep
C$ 417pp
YYZ
Toronto Pearson Intl
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl

Canada to Chicago 2021 flight deals

Cheap flights to Chicago from Canada found for this year
2 Nov - 3 Nov
C$ 319pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
6 Oct - 13 Oct
C$ 323pp
YYZ
Toronto Pearson Intl
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl
6 Oct - 13 Oct
C$ 327pp
YYZ
Toronto Pearson Intl
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl

Direct flights to Chicago from Canada

Save time with Canada to Chicago direct flight deals
2 Nov - 3 Nov
C$ 319pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
6 Oct - 13 Oct
C$ 334pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
15 Dec - 18 Dec
C$ 358pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl

Last minute flights from Canada to Chicago

Late deals on round-trip flights to Chicago from Canada, departing today and this week
2 Aug - 25 Aug
C$ 489pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl
5 Aug - 17 Aug
C$ 501pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl
5 Aug - 17 Aug
C$ 514pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl

One-way flights to Chicago from Canada

The cheapest one-way flights from Canada to Chicago
4:30 a.m. - 9:13 a.m.
United Airlines
1 stop
5h 43m
YYZ - ORD
United Airlines
C$ 227
United
9:41 a.m. - 7:41 p.m.
Delta
2 stops
11h 00m
YYZ - MDW
Delta
C$ 242
Delta
6:15 a.m. - 12:36 p.m.
Air Canada
1 stop
7h 21m
YYZ - ORD
Air Canada
C$ 247
Air Canada

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Canada</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Canada to Chicago

Can I find flights from Canada to Chicago for under C$ 377 on Cheapflights?

Yes, there are multiple flights from Canada to Chicago for under C$ 377. The cheapest flight booked recently is on Air Canada for just C$ 319, but on average you can expect to pay C$ 353.

What safety measures are being taken by airlines flying from Canada to Chicago to control the spread of COVID-19?

New policies can now be found on Alaska Airlines to help keep travellers safe while flying. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially-distanced seating (for a limited time) will work towards keeping travellers safer while flying from Canada to Chicago. Policies will vary by airline.

Which airlines flying from Canada to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Canada to Chicago have new flexible policies in place due to COVID-19. Air Canada, United Airlines, and American Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Air Canada with this kind of flexibility.

Are there direct flights from Canada to Chicago for under C$ 377 on Cheapflights?

Cheapflights has 20 direct flights from Canada to Chicago under C$ 377. A good price for a direct flight from Canada to Chicago is less than C$ 401.

Are there last-minute flights available from Canada to Chicago for under C$ 502?

There are currently 20+ open flights from Canada to Chicago within the next 7 days for less than C$ 502.

What days are direct flights available from Canada to Chicago?

Days when direct flights are available for this flight are: Tuesday.

What are the most popular airlines that fly from Canada to Chicago?

When booking a flight from Canada to Chicago, you may want to consider flying on American Airlines, Air Canada or Alaska Airlines as they are the most popular for this route.

What are the most popular routes from Canada to Chicago?

The most popular flight routes from Canada to Chicago are Toronto Pearson Intl - Chicago O'Hare Intl, Vancouver Intl - Chicago O'Hare Intl and Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl.

What are the cheapest flights from Canada to Chicago?

The cheapest flight price from Canada to Chicago is C$ 255. On average you can expect to pay C$ 797. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for C$ 358.

How long is the flight from Canada to Chicago?

A quick flight from Canada to Chicago can take about 1h 49m. Air Canada provides one of the quickest options available for as low as C$ 363. Generally, flights for this route are direct.

What are the cheapest airlines to flying from Canada to Chicago round-trip?

Currently priced at C$ 319, Air Canada will fly you from Canada to Chicago and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and United Airlines - these airlines can fly you to your destination from C$ 359 and C$ 377, respectively.

What are the cheapest airlines to fly from Canada to Chicago one-way?

One-way options have recently been found by users for as low as C$ 186 on Air Canada. Other airlines that offer cheap prices include American Airlines from C$ 206 and United Airlines from C$ 224 one-way.

Departure points for flights from Canada to Chicago

Select to see more specific information for flights to Chicago from all departure points in Canada.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Canada to Chicago.
Today's exchange rate
C$ 1 = $0.80
Flight duration
2h 13m
Average temperature for July in Chicago
29.0 °C
Avg rainfall for July in Chicago
95.0 mm

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 9 airlines flying from Canada to Chicago

The chart below displays the airlines Cheapflights users travelling from Canada to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
C$ 182 C$ 268 No cancel fee 62%
Search Frontier flights
Porter Airlines
C$ 199 C$ 299 No cancel fee 52%
Search Porter Airlines flights
Alaska Airlines
C$ 132 C$ 323 No cancel fee 75%
Search Alaska Airlines flights
American Airlines
C$ 130 C$ 363 No cancel fee 71%
Search American Airlines flights
Delta
C$ 148 C$ 373 No cancel fee N/A
Search Delta flights
WestJet
C$ 177 C$ 376 No cancel fee 60%
Search WestJet flights
Air Canada
C$ 140 C$ 376 No cancel fee 67%
Search Air Canada flights
United Airlines
C$ 176 C$ 433 No cancel fee 69%
Search United Airlines flights
Aer Lingus
C$ 289 C$ 472 No cancel fee N/A
Search Aer Lingus flights
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